Methane → 3-Phenylprop-2-En-1-Ol

HRID 363541Notes

Reaction equation

HRID 363541 reaction equation
C(O[C:9]([C:11]1[CH:16]=[CH:15][C:14](CO[Si](C(C)(C)C)(C)C)=[CH:13][CH:12]=1)=[CH2:10])C1C=CC=CC=1.[CH2:26]([O:33]C(C1C=CC=C(CO[Si](C(C)(C)C)(C)C)C=1)=C)C1C=CC=CC=1.ClCC=CC1C=CC=CC=1.[Si](Cl)(C(C)(C)C)(C)C.C>>[OH:33][CH2:26][CH:10]=[CH:9][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 5

HCID 297MethaneHCID 28928tert-Butyldimethylsilyl chlorideHCID 94242Benzene, (3-chloro-1-propenyl)-HCID 21253622alpha-Benzyloxy[3-(tert-butyldimethylsilyloxymethyl)styrene)2×HCID 21253631alpha-Benzyloxy[4-(tert-butyldimethylsilyloxymethyl)styrene]

Product 1

HCID 3083-Phenylprop-2-En-1-Ol

Procedure

α-Benzyloxy[4-(tert-butyldimethylsilyloxymethyl)styrene] and α-Benzyloxy[3-(tert-butyldimethylsilyloxymethyl)styrene] (Formula II, R1 =(tert-butyldimethylsilyloxymethyl)phenyl, R2 =benzyl). (Hydroxymethyl)styrene was prepared from (chloromethyl)styrene (a 2:3 mixture of para and meta isomers) by a sequence described in Polymer, 1973, 14, 330. It was treated with tert-butyldimethylsilyl chloride following the general directions found in Journal of the American Chemical Society, 1972, 94, 6190. Method C was used to convert the 25 resulting compound to the required alkoxystyrene: 1H NMR (CCl4) δ 0.70 (6H, s), 0.94 (9H, s), 4.17 (1H, d, J 2.4 Hz), 4.63 (3H, broadened s), 4.83 (2H, s), 7.0-7.6 (9H, m); MS (CH4) 355 (MH+, 4%), 91 (100%).

Workup

  1. additiona 2:3 mixture of para and meta isomers) by a sequence

Sources & evidence

ORD record
ord-c3a9916de90f4a3186ea455b5e3c49de
Source dataset
uspto-grants-1999_02
Patent number
US05874511

Reaction notes

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