Phenol → 2,4,6-Tris(1-phenylethyl)phenol

HRID 1709802Notes

Reaction equation

HRID 1709802 reaction equation
P(=O)(O)(O)O.C1(O)C=CC=CC=1.[CH2:13]=[CH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[CH3:21][CH:22]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[OH:35])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[CH3:36][CH:37](C1C=CC(O)=CC=1)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.[CH3:51][CH:52]([C:59]1[CH:64]=[C:63]([CH:65]([CH3:72])[C:66]2[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=2)[CH:62]=[CH:61][C:60]=1[OH:73])[C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1>C(O)=O>[CH3:13][CH:14]([C:31]1[CH:32]=[CH:33][CH:34]=[C:29]([CH:22]([CH3:21])[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:30]=1[OH:35])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[CH3:51][CH:52]([C:59]1[CH:64]=[C:63]([CH:65]([CH3:72])[C:66]2[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=2)[CH:62]=[C:61]([CH:37]([CH3:36])[C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:60]=1[OH:73])[C:53]1[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=1

Participants

9

Reactant 6

HCID 996PhenolHCID 1004Phosphoric AcidHCID 7501StyreneHCID 947634-(1-Phenylethyl)phenolHCID 953222-(1-Phenylethyl)phenolHCID 1028772,4-Bis(1-Phenylethyl)Phenol

Product 2

HCID 866882,4,6-Tris(1-phenylethyl)phenolHCID 122361152,6-Bis(1-phenylethyl)phenol

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
110 °C

Procedure

A four-neck flask with a dropping funnel, a thermometer, a condenser and a stirrer was charged with 5 g of formic acid, 4 g of 85% phosphoric acid and 28 g of phenol, and was heated up to 110° C. Into the reaction mixture was poured 63 g of styrene through a dropping funnel for 3 hours and stirred for an hour. The reaction mixture consisted of 22% of 2-(α-methylbenzyl)phenol, 12% of 4-(α-methylbenzyl)phenol, and 66% of 2,4-di-(α-methylbenzyl)phenol, when analyzed with a gas chromatography as a % area. 2,6-Di-(α-methylbenzyl)phenol and 2,4,6-tri-(α-methylbenzyl)phenol were not formed. Phosphoric acid and acetic acid were removed by washing with water. The organic layer was distilled under reduced pressure at 0.2 mmHg to give 57 g of 2,4-di-(α-methylbenzyl)phenol.

Sources & evidence

ORD record
ord-4ffd22c839b0455f9d2fedccbfacbbc6
Source dataset
uspto-grants-1990_08
Patent number
US04950810

Reaction notes

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