2-Naphthol → 1,8-Bis (2-naphthoxy) octane

HRID 1660109Notes

Reaction equation

HRID 1660109 reaction equation
[Na].[CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[OH:12].BrCCCCCCCCBr.[CH:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][C:24]=1[O:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]>>[CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[O:12][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][O:33][C:24]1[CH:25]=[CH:26][C:27]2[C:32](=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:23]=1

Participants

5

Reactant 4

HCID 86632-NaphtholHCID 783101,8-DibromooctaneHCID 5360545SodiumHCID 14718441HCID 14718441, compound

Product 1

HCID 130554851,8-Bis (2-naphthoxy) octane

Procedure

Using the method described in Example 1, the crude solids were prepared using 5.5 g (0.24 gram atoms) sodium metal, 34.6 g (0.24 mole) 2-naphthol, and 27.2 g (0.100 mole) 1,8-dibromooctane. Recrystallization from ethyl acetate gave 30.0 g, mp 128° C., and 0.8 g, mp 125°-126° C., of pure 1,8-bix (2-naphthoxy) octane. The NMR spectrum was consistent with the structure and showed the absence of impurities.

Workup

  1. customthe crude solids were prepared
  2. customRecrystallization from ethyl acetate
  3. customgave 30.0 g, mp 128° C., and 0.8 g, mp 125°-126° C.

Sources & evidence

ORD record
ord-911d231d6fb646a1a98f5ef0c38c40d4
Source dataset
uspto-grants-1981_12
Patent number
US04307077

Reaction notes

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