Hydroxyphenylacetic acid → 3,3,3-Triphenylpropyl 2-(4-hydroxyphenyl)acetate

HRID 363703Notes

Reaction equation

HRID 363703 reaction equation
[C:1]1([C:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:8][CH2:9][OH:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30][C:31](O)=[O:32])=[CH:26][CH:25]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[OH:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30][C:31]([O:10][CH2:9][CH2:8][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[O:32])=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 127Hydroxyphenylacetic acidHCID 11776TriphenylphosphineHCID 2986573,3,3-Triphenylpropan-1-olHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 537496193,3,3-Triphenylpropyl 2-(4-hydroxyphenyl)acetateYield 34%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To triphenylpropanol (3.98 mmol), 4-hydroxyphenylacetic acid (3.98 mmol), and triphenylphosphine (4.39 mmol) in dry THF (20 mL) at 0° C. under a nitrogen atmosphere, was added DEAD (4.39 mmol) in dry THF (20 mL) over 15 minutes. The reaction was stirred at room temperature for 16h and then the THF was evaporated. The residue was chromatographed on silica gel using 15-30% EtOAc/hexanes. White solid, mp=136°-138° C. (ether), 34% yield. 1H NMR δ 7.15-7.27 (m, 15H), 7.10 (d, J=8.5 Hz, 2H), 6.77 (d, J=8.5 Hz, 2H), 4.90 (s, 1H), 3.90 (t, J=7.9 Hz, 2H), 3.47 (s, 2H), 2.93 (t, J=7.9 Hz, 2H). Anal. calcd. for C29H26O3 : C, 82.44; H, 6.20. Found: C, 82.29; H, 6.24.

Workup

  1. customthe THF was evaporated
  2. customThe residue was chromatographed on silica gel using 15-30% EtOAc/hexanes

Sources & evidence

ORD record
ord-9710680de8bf4758b2019c971af65a58
Source dataset
uspto-grants-1999_02
Patent number
US05874436

Reaction notes

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